User:Aliaksands/Silylation: Difference between revisions
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[Protection overview and mechanism is complete on the current page] |
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Due to the strength of the Si-F bond, fluorides are commonly used to deprotect silyl groups via an SN2 mechanism.<ref name=":0">{{Cite book |last=Clayden |first=Jonathan |title=Organic chemistry |last2=Greeves |first2=Nick |last3=Warren |first3=Stuart |date=2012 |publisher=Oxford university press |isbn=978-0-19-927029-3 |edition=2nd |
Due to the strength of the Si-F bond, fluorides are commonly used to deprotect silyl groups via an SN2 mechanism.<ref name=":0">{{Cite book |last=Clayden |first=Jonathan |title=Organic chemistry |last2=Greeves |first2=Nick |last3=Warren |first3=Stuart |date=2012 |publisher=Oxford university press |isbn=978-0-19-927029-3 |edition=2nd |location=Oxford}}</ref> The aliphatic chains of the amine in tetrabutylammonium fluoride (TBAF) help incorporate F<sup>-</sup> into organic solvent. <ref>{{Cite book |title=Encyclopedia of reagents for organic synthesis |date=1995 |publisher=Wiley |isbn=978-0-471-93623-7 |editor-last=Paquette |editor-first=Leo A. |location=Chichester ; New York}}</ref> <blockquote>[Image: Deprotection reaction scheme.] |
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[Image: Deprotection reaction mechanism.]</blockquote> |
[Image: Deprotection reaction mechanism.]</blockquote> |
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Revision as of 06:51, 4 November 2024
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Lead
Protection Chemistry
[Protection overview and mechanism is complete on the current page]
Due to the strength of the Si-F bond, fluorides are commonly used to deprotect silyl groups via an SN2 mechanism.[1] The aliphatic chains of the amine in tetrabutylammonium fluoride (TBAF) help incorporate F- into organic solvent. [2]
[Image: Deprotection reaction scheme.] [Image: Deprotection reaction mechanism.]
Modifying Reactivity
Alkyl substituents with higher steric bulk tend to decrease reactivity and consequently increase the protecting abilities of the silyl group. Bulkier groups become more difficult to remove and require more strenuous conditions for deprotection.[1]
[Image: Common silyl groups, increasing left to right in steric bulk]
Enolate Trapping
Silylation can also be used to trap reactive compounds for isolation and identification uses.[1] A common example of this is reacting a silyl chloride to trap enolates. Since enolate-forming reactions can generate unwanted organic or salt byproducts, silylation is a way to isolate reactive enolates.
[Image: Isolation of a kinetic enolate into an enol silyl ether] [Image: reformation of kinetic enolate]
Silylation affords an enol silyl ether which can be characterized or stored. The original enolate can be reformed upon reaction with an organolithium, or other strong base.
References
- ^ a b c Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). Organic chemistry (2nd ed.). Oxford: Oxford university press. ISBN 978-0-19-927029-3.
- ^ Paquette, Leo A., ed. (1995). Encyclopedia of reagents for organic synthesis. Chichester ; New York: Wiley. ISBN 978-0-471-93623-7.